


In Too Deep

by songofhell



Series: In Too Deep [1]
Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2015-03-08
Updated: 2015-12-27
Packaged: 2018-03-16 21:13:19
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 13,892
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3502964
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: <blockquote class="userstuff">
              <p>How would things be different if Dean met Crowley before Abandon All Hope? What if Dean got close to him before realizing what he was? Can Dean treat him like any other demon when the truth comes out? Or is he in too deep?</p>
            </blockquote>





	1. Distraction

Dean didn't look up from his beer as he heard the stool beside him be pulled out and someone sat down next to him at the bar. He didn't know why the newcomer had decided to sit next to him rather than take one of the other many empty stools, and honestly, he didn't really care right now. He had enough to deal with at the moment.

"What will it be?" the bartender asked.

The man beside Dean spoke in a rough, British accent as he ordered two of one of the most expensive drinks there.  _'Stuck up prick,'_  Dean thought to himself before the drinks were set on the bar and one was slid in his direction.

"This one's for you, handsome. You look like you need it."

Dean looked up in surprise, finally taking in the appearance of the other man. He was older than he was, and shorter, but he had an air about him that made him seem important, despite his height. Maybe it was the expensive black suit, or the way his mouth was turned up in a slight smirk, or the confident way in which his hazel eyes met Dean's. Whatever it was, it certainly worked. Even the slightly thinning brown hair looked good on him.

"Do you buy a drink for everyone you meet, or do I just look that pathetic?" Dean asked, eyeing the expensive liquor skeptically.

"Pathetic isn't exactly the word I'd use." He brought his own drink up to his lips, taking a small sip. "Care to talk about it?"

Dean didn't answer at first, taking a drink to buy himself some time. He had to admit, it was one of the best drinks he had ever had by a long shot. And this guy had been right about one thing – he did need it.

"Come on," the man urged. "You have the look of a guy who just caught his girlfriend cheating."

"And what do you care?"

"I don't." He shrugged. "But I can tell when someone needs to talk; and you, darling, need to talk."

Dean sighed, taking another drink. The guy had just bought him the most expensive drink of his life – he supposed it wouldn't hurt to talk. "It's just… family stuff."

"So… you just caught your mom cheating on your dad, then?"

He gave a hollow laugh. The sentence sounded so ordinary and out of place in his life. "They're both dead, so that's one thing I don't have to worry about. And actually, I'm kind of glad they aren't here to see everything that's going on now."

"So, it's a sibling, then. A little brother or sister has gone and done something stupid, and you're trying to set them straight."

"My little brother," Dean confirmed with a nod.

"What's he into? Drugs? Prostitution?"

Hmm… not too far off, actually. "You're right on the first part. It's just one girl, though."

"And you think she's a bad influence?"

"She's who got him addicted in the first place. And she doesn't even give a damn about him. I don't know what exactly she's after, but it's not what she says it is. And he can't see it. I've tried to talk to him about it, but-"

"But little brother wants to make his own decisions. You know, if you can't sway him, you may just have to sway her."

"Yeah, that's not going to be that easy."

"Everyone has their limits. Find hers. I'm sure you'll agree that there's no such thing as too far when it comes to protecting family."

They guy had a point, and he really did want to kill Ruby, there was just one problem. "Sam will never forgive me."

"And what's worse? An angry brother? Or a fucked over one?"

Once again, an excellent point. He didn't like Sam being mad at him, but at least it was something he could live with. "I'll consider that."

"I suggest you do. In the meantime… I think you are in need of a distraction."

Dean arched an eyebrow, unsure of where he was going with this. "Yeah?"

"If your brother's getting some, why not you? See anything you like?"

His eyes locked with Dean's once again, and Dean found that he couldn't look away. Was this going where he thought it was? He had never been with a guy before, but that wasn't to say that he had never thought about it, that guys never turned his head. And this guy definitely did. Unable to stop himself, he began to wonder what it would be like to have sex with him, to have those lips moving over him, him thrusting inside him.

Dean was suddenly aware of the fact that he had been staring at him for far too long, and now he had another growing problem that was going to become apparent once he stood up. If not sooner… the other man's eyes flickered down to Dean's crotch before he met his eyes again, his smirk becoming more prominent.

 _Why did the dick have to be so damn confident?_  Dean thought furiously as his cheeks turned a light pink.

"I suppose that answers that question. I have a room at the hotel next door, if you would care to join me?" He got to his feet, grabbing the black, wool coat he had draped over the stool beside him, and pulling it on.

Dean hesitated. Was this really a good idea? There was a feeling in the pit of his stomach that was normally a red flag, but the alcohol made that easier to ignore. "I never got your name."

"Roderick."

"Dean," he supplied as he got to his feet. "Lead the way."

Roderick put some money down on the bar, nodded at the bartender, then made his way out the door, Dean following in his wake. The hotel that Roderick was staying at was far nicer than any of the ones that he and Sam had ever stayed in, and on top of the already higher quality, Roderick was staying in the penthouse. Dean wondered just how loaded this guy was and what he must think of him.

"Just to be clear," Dean spoke up as Roderick hung his coat up and held a hand out for Dean's. "I'm not looking for any kind of charity. Or pity, for that matter."

Roderick arched an eyebrow, taking a step closer to him. "Is that what you think this is, Dean?"

"I don't know, I just want to make sure I'm understood."

"Oh, I understand you perfectly."

Dean opened his mouth to say that he very much doubted that, but before he could make a sound, Roderick's lips were on his, rough and demanding, and everything that Dean had hoped for. He moaned despite himself as he hesitantly brought his hands up to rest on Roderick's hips. The other man was far from hesitant, though, as he pushed Dean back against the wall, one hand fisting in his short hair as the fingers of the other dug into his hip.

"Damn," Dean breathed when they finally broke.

"Have you ever been with a man before, Dean?" Roderick asked, eyeing him thoughtfully, and Dean very much felt as though he were being seized up.

"No," he admitted after a second's hesitation.

Roderick nodded once and Dean knew that he had already suspected the answer. "I'm normally not exactly – gentle in the bedroom," he warned. "If anything's too much, let me know."

Dean nodded, grateful for that. At least he was a decent guy, even if he was a bit of an arrogant dick.

"Now then…" Roderick continued, his hands trailing over Dean's sides in a way that was driving him crazy. "Let's get you out of these clothes and into bed."

Dean smirked, starting to adjust to the situation. "About time." He let his jacket drop from his shoulders and threw it over the coatrack. In a burst of confidence, he grabbed Roderick by his tie and pulled him in for a kiss. Their lips moved against each other fiercely as Roderick's hands began pushing up Dean's shirt, breaking the kiss to pull it over his head and toss it aside. He then slid off his own blazer, adding it to the rack as Dean pulled off his tie.

"I suggest that we move our activities to the bedroom," Roderick said as his hands ran over Dean's chest, lingering for just a second on his tattoo. "It will be far more comfortable, and I do want you to enjoy yourself."

Dean grinned. "After you, then."

Roderick hooked a finger into the belt loop of Dean's jeans as he started for the bedroom, pulling Dean behind him, who had rarely felt so turned on. As soon as they reached the bedroom, they both quickly stripped out of the rest of their clothes, and then Roderick practically threw Dean down onto the bed.

Roderick took a moment to stand over Dean, admiring the younger man spread before him. "Damn, I was right about you. Absolutely gorgeous." He leaned down, his lips gliding along Dean's thigh and then ghosting over his cock.

Dean moaned, his hips arching off the bed slightly as he silently begged for more.

Roderick just chuckled, his breath torturous against where Dean so desperately needed more. But Roderick continued to move his lips up Dean's body, straddling him as his tongue flicked over his nipple before he got to his collarbone, where he bit down, almost hard enough to draw blood.

A deep groan tore from Dean's throat as his hand came up to tangle tightly in Roderick's hair. "Please…" he breathed, desperately grinding his hips up in an attempt to get some friction.

"Please what?" Fingers trailed down Dean's stomach, teasing just above his cock.

"Stop being such a tease."

Roderick chuckled. "You just met me, so I'll let that slide. But I should warn you, I do not like demands, and would normally punish a mouth like that."

Dean couldn't deny that he was a bit tempted by that, but he decided to play it safe for now. "What would you prefer I say?"

"I would prefer you  _beg."_

"Not my style."

"Then I hope you aren't expecting to get anything from me."

Determined not to give in, his hand dropped from Roderick's hair and moved to his own cock. Before he could do more than brush his fingers against his erection, though, Roderick growled and wrapped a hand tightly around his wrist, holding it down on the bed.

Dean's eyes narrowed. "Bastard," he muttered.

There was a dangerous gleam in Roderick's eyes as his other hand shot up and wrapped around Dean's neck, effectively cutting off his airflow. "Excuse me?" he hissed. "I don't have to do anything for you. I can use you for my own pleasure and then toss you aside like a chewed-up toy. Maybe I didn't make it clear –  _I'm_  in charge here, so if you want something, you had better ask nicely."

Dean gasped for air as Roderick's grip finally loosened slightly. "I'm sorry," he gasped. Damn this guy, he had never been so turned on in his life. "Please, Roderick, please, I need some friction. Please…"

Roderick smirked, satisfied, as his hand slid to the side to grip Dean's shoulder as he ground down against him, their cocks sliding together.

"Fuck," Dean groaned, pushing his hips up as the hand that wasn't still being pinned down gripped Roderick's ass, pulling him even closer.

Roderick lavished Dean's neck with kisses and bites as his hand finally released Dean and instead wrapped around the both of their cocks. He started pumping slow, but he gradually increased the pace, groaning against Dean's skin.

Dean ran his newly freed hand all over Roderick's body, wanting as much of him as he could get. He drug his nails down his back, hoping to leave some kind of mark to repay the many that he knew Roderick was leaving on his neck. And Roderick was in the same frame of mind as his hand slid down from Dean's shoulder and began exploring his chest.

Eventually, Roderick stopped, his hands leaving Dean as he reached behind him, to the bedside table.

"What…?" Dean started to asked, still attempting to grind his hips up against him.

"I don't know about you, but I've had just about enough foreplay." He brought his hand down again and ran is fingers, now covered in lube, at Dean's entrance.

In all honesty, Dean was a bit nervous. Was he seriously going to let this guy fuck him? But then Roderick slipped a finder inside him, and Dean arched back with a moan. Yes, he definitely was.

After a minute, Roderick added another finger, and then a third. He watched Dean's expression hungrily as he writhed beneath him, moaning shamelessly. "Do you want me to fuck you, Dean?" he finally asked softly.

"Yes!" Dean gasped, all doubts chased away by Roderick's amazingly skilled fingers inside him.

"Oh, come on. You're going to have to do a better job than that."

"Please, fuck me! I need you inside me. Please!"

"Well… since you beg so beautifully…"

He started to reach up for the lube, but Dean was already there, scooping some up. He warmed it up in his hands some before reaching down and beginning to spread it over Roderick's cock, causing him to give a low groan. Once he was done, his hands slid to his hips, pulling him closer.

Roderick lined himself up with Dean and then thrust in slowly, being as gentle as he could. Dean's hands gripped Roderick's hips with bruising force as he made a sound between a groan of pleasure and a hiss of pain. Roderick was  _very_  well endowed, and Dean wasn't quite prepared for the sensation of having him inside him. He was stretching Dean, filling him up completely, and damn, he felt amazing. He gave Dean a minute to adjust before he started moving. He took it slow, making sure that he didn't hurt Dean, then he gradually began to increase his pace.

As he started to move faster, Roderick's lips returned to Dean's chest, occasionally biting down hard to quiet his moans. Dean, on the other hand, couldn't hold back his moans and shouts, and though he was being embarrassingly loud, he was far from caring right now. This was some of the best sex he had ever had, and he knew that he wouldn't be able to make it very long. Sure enough, almost as soon as Roderick reached down and began pumping his cock, the pleasure became too much for him and he came all over their stomachs and Roderick's hand.

Roderick got in a few more thrusts before he finished with a deep groan, emptying himself into Dean before rolling to the side. "That… was better than I had anticipated."

Dean looked over at him with a raised eyebrow. "Did you not think I would be very good?"

"Oh no, I thought you would be amazing, and you still exceeded my expectations."

Dean smirked proudly. "Well, you're not so bad yourself."

"No so bad? Is that all I get? After the sounds you were making, I had better get some higher praise than that."

Dean rolled his eyes. "I think your ego's big enough."

"Rude."

"But true." He scooted closer, placing a kiss to Roderick's shoulder.

Roderick smiled and wrapped an around him. "Get some sleep, Dean. I'm sure you need it."

He really did need it – not just because of the drinking and the sex, though those added to it, but he really hadn't been sleeping much lately – he hadn't been able to. After that, though, he was out almost as soon as he let his eyes close.

* * *

When Dean opened his eyes, it took him a minute to remember what had happened the night before. Right, he had hooked up with a hot, British guy and had the best sex of his life. He vaguely wondered if sex with men in general was that great, or if was just him.

Roderick wasn't in bed, and after scanning the room for a second, Dean spotted him standing by the window, looking outside. He was in the same suit he had worn at the bar the night before and he had a phone to his ear.

"I was under the impression that I am still permitted to go out and enjoy myself on occasion," Roderick spoke. His voice was polite, but Dean could sense the irritation. "As long as I come crawling back to you, of course." He was silent for a moment as whoever was on the other end of the phone replied. "That is not what I mean, my lady, I assure you. I was merely referring to the fact that I do work for you, whatever my rank, and I will always be here to serve you. I am loyal to you, as always…. Yes, I realize that, but I didn't believe that I had any duty last night. There was nothing that I could have done…. Then, forgive me, but I don't really see…. I just hit up a bar and found a hook-up…. No, he's no one important."

Dean wasn't sure why exactly that felt like a slap; this was just a random hook-up, of course he was no one of importance to this guy.

"Not yet," he continued. "Of course I want this! Who wouldn't?... I'm worried merely for your well-being…. As I said, I didn't see the harm in taking the night off…. Of course, I will be there right away." He pulled the phone away from his ear and hung up. "Ignorant bitch," he muttered.

"Who was that?" Dean asked, pushing himself into a sitting position.

Roderick spun around, his eyes wide. "My boss…. How much of that did you overhear?"

"Enough to get that she doesn't want you to have any free time."

He chuckled. "Oh, you have no idea. All of us have to be entirely focused on this great idea of hers that is going to end up destroying us all."

"And you've talked to her about this?"

"If I do, I'll be – fired." He sighed. "Anyway, I have to go – business calls. Feel free to use the shower or whatever and let yourself out. I hope to run into you again sometime." Before Dean could say or do anything, he walked out the door.

Hope to run into you again sometime? What kind of a goodbye was that? He didn't want his number or anything?

Dean sighed as he got out of bed. The best sex of his life and he would probably never see the guy again. Of course.


	2. Mine

A couple months had passed since Dean's one-night stand with Roderick, and quite a bit had happened since then. Lucifer had been let out of the cage, thanks to Sam's trust in Ruby, and now the two of them had gone their separate ways. It was safe to say that he was in an even worse place now than he had been in before. So it was no surprise that he was now sitting at a bar, downing whiskey.

"Still drowning your sorrows in cheap liquor?" a familiar voice spoke from behind him.

Dean spun around on his stool to see Roderick standing behind him. "What are you doing here?" the words fell from Dean's mouth before he had a chance to think about them.

Roderick raised an eyebrow. "This bar is open to the public, is it not?"

Dean's cheeks took on a faintly pink tinge. "Yeah, I just… didn't expect to see you here." Or anywhere ever again, really. After all, what were the odds?

"You've seen me here before," he pointed out, and it was true that this was the same bar where they had first met.

"Yeah, but you were staying in a hotel – you don't live in the area."

"Well, I'm back. And it is true that this isn't the kind of place that I would normally choose to frequent. The last time I was only here for business."

"And this time?"

Roderick smirked slightly. "I was hoping to see you."

"Oh." Dean didn't know what to say. With the way that Roderick had left last time, he had figured that he never wanted to see him again. He had rarely been so happy to be wrong.

"May I join you?"

"Yeah," Dean answered immediately.

"Good." Roderick took the stool next to him and ordered two of the same drink from last time, once again scooting one over to Dean.

"You should let me buy you a drink sometime."

"I don't think I would like what you would buy. I have very high tastes."

"I've noticed," Dean said as he raised his glass to his lips and took a drink. "So what business were you doing here before? I thought your boss didn't even want you to be here."

"She didn't. The work wasn't for her, it was against her. I was seeing a rival, hoping he could take her down."

"And did it work?"

"No. She got what she wanted and now we're all screwed."

"I know the feeling."

"So it appears. Things not work out with your brother?"

Dean sighed. "No. We're… not really talking now."

"And how's that supposed to fix anything?"

"Look, I can't really explain, but he did some stuff, and I just can't look at him the same way anymore."

"And instead of helping him, you're alienating him? Makes sense."

"You don't understand."

"Maybe not, but when I met you, you seemed to care about your brother a lot more than that."

"I do care about him, but this is the right thing, and you're not changing my mind on it."

"Fine. However, I do believe that statistics show that most recoveries happen with the aid of supportive family members. Just something to think about. But I digress, it is your family, your decision, so let's move along. You didn't think you'd see me again, did you?"

"How could I expect to when you just left with no way to get in contact again?"

Roderick regarded him thoughtfully for a moment, a touch of amusement in his expression. "Did I hurt your feelings?"

Dean glared at him. "You're an asshole, you know that?" He finished his drink before getting to his feet. "And I'm not going to sit here while you insult me." He wasn't going to let him think he had some kind of hold on him that he could lord over him. Yes, he had wanted to see him again, but he could still walk away.

Roderick chuckled. "Would you rather be laying in my bed?" He stood up as he placed some money down on the bar. "Same room as last time, if you're interested." He took a step closer to Dean and squeezed his ass as he leaned in to whisper. "And I sincerely hope you are. After all, you are the reason I'm here."

He didn't wait for Dean's reaction before he walked out of the bar, leaving Dean staring after him for a moment. Dammit, how could he say no to that? He sighed and then walked out the door and to the penthouse of the hotel he had been in only once before, finding the door to the room open.

"You can shut that behind you," Roderick said from the couch as Dean walked inside.

Of course Roderick would know he would come. Dean doubted that a guy like him even knew what rejection was like. He closed the door behind him and hung up his jacket before walking over to the couch and sitting down beside Roderick.

"Drink?" Roderick offered, holding up a bottle of scotch.

"Sure."

He poured Dean a glass and passed it to him before taking a drink of his own. They drank in silence for a moment before Dean decided to ask the question he was puzzling over. "Can I ask you something without you being the cocky son of a bitch you always are?"

"You can try," Roderick answered with a chuckle.

"Why did you come back?"

"I wanted to see you again."

"And it was too much trouble for you to ask for my number before you left?"

"It's not what I do. Of course, I've never wanted more than one night with a person before, so it's never been necessary."

Dean blinked in surprise. "What makes me different?"

Roderick shrugged. "Excellent question. But whatever the reason, I haven't been able to get you out of my head, and so, here I am."

Dean smiled, scooting a bit closer to the other man. "So, what exactly have you been thinking about me?"

Roderick finished his drink and set the empty glass down on the table before turning slightly to face Dean more fully. "That I can't wait to have you beneath me again," he spoke in a low voice. "I love the sound of you begging, your moans…. I want to make every inch of you mine."

Dean swallowed, setting his drink down so that it wouldn't show that his hand was shaking slightly. "So, what are you waiting for?"

He grinned. "For you to be a bit more perceptive and use that brain of yours."

Dean blinked in confusion, trying to figure out what he meant by that. "Perceptive about what?"

"What did I just say, Dean?"

He ran over the last few things Roderick had said in his mind.  _Oh._  Fucking bastard.

He crawled closer to the other man, stopping when he was just shy of sitting in his lap. "Please, Roderick," he spoke softly, holding eye contact. "I want you." He couldn't believe that this guy was getting him to beg for him  _again,_  but he couldn't deny how much he really did want him.

Roderick appeared unfazed as he simply arched an eyebrow. "Do you now?"

"Yes. I haven't been able to get you out of my mind either. I want to feel you take me again. I want you to make me yours."

At that, Roderick's eyes darkened and he grabbed Dean by his shirt, pulling him roughly into a kiss. Dean moaned against his lips, his hands immediately pulling at the other man's clothes, wanting them off.

Roderick captured Dean's bottom lip between his teeth before pulling back slightly. "Dean, you should know, when I say I want to make you mine, I don't mean that lightly. I can be very possessive. And I am  _not_  a good person."

"Yeah, well, neither am I. I don't care. And you can be as possessive as you want." He didn't know what it was about Roderick that made him want him so much, but he did know that he had never been unable to get a one-night stand out of his head before. And sure, Roderick could be a dick, but so could he. How bad of a guy could he really be?

Roderick cupped the side of Dean's face in his hand. "You might end up regretting that."

Dean shrugged. "It's my decision. You'd just better leave me with your number this time."

He grinned. "Deal."

* * *

Dean didn't get to see Roderick as often as he would like. After all, Roderick was always busy for whatever cooperation it was he worked for – he never gave Dean the details, only said that he was very high up in it – and Dean was busy hunting and trying to find a way to kill Lucifer. They stayed in contact, though, and Dean was debating on whether or not he should tell his brother, who he was once again hunting with, that he had a boyfriend – not that they had ever used that term.

_'_ _I miss you,'_  Dean texted to him one day as he laid on Bobby's couch.

It was only a minute before he got a response.  _'I'm not surprised.'_

He grinned. He was starting the like the smart-ass comments he made. Well, the more time he spent with him, the more he liked him altogether. Which could be a problem. It wasn't generally good for hunters to have attachments, particularly of this kind. He knew that, and yet here he had gone, being an idiot, and gotten himself into a relationship. And now reality was setting in, and what was he supposed to do? Call it off? The very idea made it feel as though a weight dropped in his stomach. There was no way he could bring himself to. Tell him the truth, then? Let him make his own decision? It wasn't something that he was exactly in favor of, but he really liked Roderick, and if anyone deserved to know, he did.

It was a couple of days later when he made this decision and shot him a text.  _'When can we meet up? There's something we need to talk about.'_

Dean wasn't sure if Roderick's reply really did take longer than normal, or if it just seemed that way because he was nervous.  _'Make that two things. Are you free tomorrow?"_

Two things? Great.  _'I should be.'_  If everything worked out.

_'_ _Good. See you then.'_

Dean stared at his phone for a few minutes. How was he going to tell him? And how would he react? Would he even believe him? And what did he want to talk to him about?

He was pulled from his thoughts as his phone started to go off, notifying him that Cas was calling.

"Cas?" he answered.

"Got him. The demon Crowley is making a deal; even as we speak, it's going down."

Good. Then hopefully, they would be able to take care of everything with Crowley tonight, get the Colt back, then he would be able to see Roderick tomorrow. His stomach tightened slightly. What could go wrong?


	3. Truth

Dean carefully laid the rug back down, concealing the devil's trap he had just drawn on the underside of it. He nodded to Sam as he straightened up, aiming his gun down the hallway as Sam clutched his knife. They had trapped enough demons, so this really shouldn't be difficult, even if this time they were in the demon's own house. Dean just hoped that this Crowley still had the Colt.

He heard footsteps approaching and he tightened his grip on his gun slightly. And then the demon rounded the corner and Dean's jaw dropped. What the…? "R-?" he started to ask, but he was interrupted before he could get the name out.

"It's Crowley, right?" Sam asked.

No, he couldn't be. Unless he was possessed. Dean felt a panic rising in him that he fought to push down. Why would Crowley just happen to possess Roderick, of all people? Was it for his benefit? But how did he even know about them? No one knew, not even Sam. And this was not the way that he wanted his brother to find out. He had to pretend like he didn't know him, and hope that Crowley, who Dean knew had access to Roderick's memories, would do the same. But how could he just stand here and pretend when all he wanted to do was make sure Roderick was alright?

"So," Crowley spoke. "The Hardy Boys finally found me. Took you long enough." His eyes flickered to Dean, his expression unreadable, before he glanced down at the rug. He bent down and picked up the edge, looking at the devil's trap underneath. "Do you have any idea how much this rug cost?"

Despite himself, Dean got a faint urge to laugh. That sounded just like something Roderick would say, and for a moment it was easy to forget that the man in front of him was just using his body as a puppet. Still, the entire time they were there, it was hard to differentiate Crowley from Roderick, and Dean wanted to kill him all the more for it, even though the bastard did willingly give them the Colt and divulged that he wanted them to kill Lucifer.

When Dean left Crowley's that night, he was sure of one thing, he had to get Roderick back, and he had the beginnings of an idea as to how to go about it. From what he had seen of Crowley, he seemed to have the sense of humor that would enjoy the irony of showing up where Dean and Roderick had agreed to meet the next day. There was no guarantee, but it was worth a shot.

So the next day found Dean knocking on the door of the penthouse of the nicest hotel in the area. He just had enough time to think,  _'Please be here,'_  when the door was pulled open to reveal Crowley standing there with the same unreadable expression he'd worn when he had seen him at his house.

"I didn't think you'd come," he admitted.

"Yeah, well, I need some answers." Dean shoved past him, into the room.

"Of course," he sighed as he closed the door and walked over to the table. "Would you like a drink?"

"No."

Crowley just nodded as he poured himself a glass of scotch, the same kind Roderick always drank, then walked over to take a seat on the armchair. "Have a seat, Dean."

"I'm good."

"Alright…. Ask away, then."

"I talked to Roderick just yesterday, unless that wasn't really him, either way, you chose to possess him fairly recently. Why him? You had to know about us. What this just for-"

"You think I'm possessing Roderick?" Crowley interrupted, vague surprise on his features.

"You are."

He sighed as he set his drink down as rose to his feet. "No, Dean, I'm not." He took a step closer, but Dean retreated a step. He didn't normally back away from demons, but Crowley was making him sick. "I've had this meatsuit for years, and its original occupant is long since dead – I don't like sharing. Roderick was my middle name as a human, it's what I use when I don't want people to know who I am."

Now Dean really felt like he was going to be sick. "You're lying."

"I have never lied to you Dean. Unless you're counting my name, but that was only a half-lie."

"You really expect me to believe that?"

"Expect? No. But it is the truth."

Dean shook his head, looking away from the demon in front of him. Roderick wasn't even real, it was all just some sick joke by this demon.

"Dean, I-" Crowley reached for him, but Dean jerked his arm away.

Crowley had played him, but he wouldn't get away with that anymore. Dean quickly pulled out the demon knife and pressed it against Crowley's throat. The demon took in a sharp breath, but made no attempt to move, maintaining eye-contact with Dean. "I don't ever want to see you again," Dean growled. With that, he turned on his heel and stormed out the door, slamming it behind him. He could have sworn that he heard a crash in the room as he took off down the hall, but he didn't care. He was done.

Of course, he should have known better than that. Crowley was a demon, Dean was a hunter, there was a good chance that they would run each other again down the road. And sure enough, it happened far too soon.

Dean was on the phone with Bobby as he and Sam drove through West Nevada. They were trying to track down Pestilence, but they had just about nothing to go on. Dean was just hanging up the phone when an all too familiar voice spoke from the backseat.

"Say… I've got an idea."

Dean slammed on the brakes as Sam plunged his knife into the backseat.

"Did you get him?" Dean demanded, ashamed of himself for not being sure what he wanted the answer to be.

"He's gone."

A second later, Crowley was tapping on Sam's window. "Fancy a fag and a chat?"

They both got out of the car, Sam stalking towards Crowley with deadly intent, the latter of which quickly backed up towards Dean.

"You're upset. We should discuss it. Not here, but-"

"You want to talk?" Sam demanded as Dean worked on sorting through his emotions. Crowley had lied to him, and then betrayed all of them, getting Ellen and Jo killed, but there was still a part of Dean who saw the man he had once pretended to be. "After what you did to us?"

"After what I – what I did to you?! I gave you the Colt!"

"Yeah, and you knew it wouldn't work against the devil!"

"I never!"

"You set us up. We lost people on that suicide run – good people!"

"Who you take on the ride is your own business! Look, everything is still the same. W-we're all still in this together."

"Sure we are."

Crowley managed to teleport to the other side of Sam, just in time to avoid being stabbed. He turned his attention to Dean, for the first time acknowledging his presence. "Call your dog off – please."

Dean's expression hardened. "Give me one good reason."

"I can give you Pestilence."

That brought Dean up short. "What do you know about Pestilence?"

"I know how to get him. That's got your interest, doesn't it?"

"Are you actually listening to this?" Sam demanded.

"Sam-"

"Are you friggin' nuts?!"

Maybe. "Shut up for a second, Sam!"

"Shut up, the both of you!" Crowley cut in. "Look...I swear... I thought the Colt would work. It's an honest mistake. It's all part of the learning process. But nothing's changed. I still want the devil dead. Well...one thing's changed. Now the devil knows that I want him dead. Which, by the way, makes me the most buggered son in all of creation."

He thought the Colt would work…. Not that that made any difference. He had still lied to him, used him. "Holy crap," Dean sighed in exasperation. "We don't care."  _Who are you trying to convince?_  a small voice in the back of his mind spoke.

"They burnt down my house!" Crowley shouted. "They ate my tailor! Two months under a rock, like a bloody salamander! Every demon on hell and earth's got his eyes out for me! And yet... here I am... last place I should be – in the road, talking to Sam and Dean Winchester, under a friggin' spotlight!" He pointed up and the street light exploded. "So come with me," he continued more calmly. "Please. Do you want the horsemen rings or not? Yes, I know all about that. Shall we?"

"Dean, you're not…?" Sam started.

Dean sighed as he turned to his brother, hating himself for what he was about to say. "He may be the best chance we've got."

Crowley grinned. "Shotgun!"

Sam glared at him. "Not happening."

Sam got into the passenger's seat before Crowley could make a move towards it. Dean got back into the driver's seat without another word, not all that surprised when Crowley teleported into the backseat.

"We can go to where I'm staying to chat," Crowley said, leaning forward. "Just continue going down this road."

Dean tried his hardest as he drove to ignore the fact of who was in the backseat, but it was hard when his voice brought back a rush of memories, when sometimes he would point and his arm would brush against Dean's. He was glad when they finally arrived, though the place certainly wasn't what he was expecting. It was a dump, worse even than some of the motels he had had to stay at on the road.

"Here we are," Crowley said with a sigh as they stepped inside. "My life on the lam. How the mighty have fallen. Single-pane glass, used contraception in the fireplace. The water damage alone-"

"My heart's bleeding for you," Dean interrupted, wanting to just get this done and then leave. "Now, how do you know about the rings?"

"Well, now… I've been keeping a close eye on you lot."

"We got hex bags," Sam pointed out. "We're hidden from demons."

"All but one. That night you broke into my house, my valet hid a tracking device in your car – a magical coin that easily trumps your little bags o' bones. It allows me to hear things, too – and, my, the things I've heard. So you want to cram the devil back in the box? Cunning scheme. I want in."

Dean's blood was boiling. Not only had this guy screwed with him life, but he had been spying on them? "You son of a bitch," he hissed. "You said you could get us Pestilence."

"Well, now… I don't know where Pestilence is per se. But I do know the demon who does. He's what you might call the horsemen's stable boy. He handles their itineraries, their personal needs. He's who you want – believe me. He'll tell us where Sneezy's at."

"Well, how do we get him to spill? Rip out his toenails?"

"No. Nuts at his pay grade don't crack. We bring him here, then I sell him."

"Sell him?" Sam asked.

"Please. I've sold sin to saints for centuries. Think I can't close one little demon?"

"All right," Dean said, trying to keep this moving along. "So where's this demon of yours?"

"He's currently acting as head of Niveus Pharmaceutical, clearly doing some job for Pestilence. So then, shall we?"

"Give us a minute." Sam grabbed Dean by the arm and pulled him aside. "Why are we even listening to him, Dean?" he demanded. "This is totally insane."

"I don't disagree," Dean sighed. Of course he didn't want to do this, but what other choice did they have?

"One big happy family, are we, then?" Crowley cut in. "Fantastic."

Dean reluctantly turned to him. "You ready to go?"

"Yes. Yes. I am." He started to turn to go. "Sam, keep the home fires burning."

"What are you talking about?"

"Sam's not coming."

Dean felt the knot in his stomach, which had been present since Crowley appeared, tighten. His first concern wasn't that Sam was going to be left behind, it was that that meant he would be in the car alone with Crowley – something he would give almost anything to avoid.

"And why the hell not?" Sam demanded.

Crowley turned to him with narrowed eyes. "Because I don't like you… I don't trust you… and – oh, yes – you keep trying to kill me!"

"There's no damn way. This isn't gonna happen!"

"I'm not asking you, am I? 'Cause you're not invited. I'm asking you." He pointed to Dean. "What's it gonna be?" He glance at Dean's clearly reluctant expression and scoffed. "Gentlemen… enjoy your last few sunsets."

"Wait," Dean sighed. "I'll go." He glanced back at Sam. "What can I say? I believe the guy."

Crowley grinned and Dean followed him outside, getting into the Impala. It was uncomfortable, to say the least. He tried not to look at Crowley, but every so often he found himself glancing over at him – he was always staring out the side window, an uncharacteristically blank expression on his face. Dean was beginning to hope that they may not have to say anything to each other, but then Crowley spoke in a soft voice.

"I was going to tell you, you know – that next day. It might have gone differently if I had told you myself."

"Doubt it," Dean spat, his grip on the steering wheel tightening.

Crowley looked over at him. "I never meant for any of this to happen. I had just gone to the bar to talk to you-"

"I thought you said you were there on business."

"I was. My business was concerning you. I thought that was obvious."

"You said that you wanted to see a competitor. How the hell is that concerning me?"

"A competitor?" Crowley shook his head slightly. "You can be really thick sometimes. I worked for  _Lilith._  I wanted her taken down."

For a second everything seemed to fall into place, but there was still one problem… "You never even mentioned Lilith."

"You're right. We talked about Ruby. And if you recall, I advised you to do whatever it took to get rid of her."

"You could have been a little more direct about it!"

"You wouldn't have believed me. I think it's pretty obvious just how much you trust demons. I told you as much as I could without you getting suspicious."

Dean didn't know what to say for a minute. It actually did make since. So… could Crowley be telling the truth? "So where exactly did sleeping with me fit into your grand plan?"

Crowley sighed. "It didn't. That just kind of happened."

"Just kind of happened? You invited me back to your room, you'd been flirting with me the entire time."

"I flirt, that's not exclusive to you. And then I saw that you were interested and I seized the opportunity. Can you really blame me?"

"Yes. That was more than seizing an opportunity, you came back, toyed with me."

"I told you why I came back and I wasn't lying," he argued, a bit of irritation seeping into his voice. "When I slept with you the first time, I had no intention of anything else. I had an opportunity to have sex with the infamous Dean Winchester, and I had to take it. But it was different than I had expected. I told you that you were the one person I couldn't get out of my mind, and I meant it. I tried having sex with others, but I kept thinking about you. So yes, I came back. I knew it was possibly the stupidest decision I had ever made, but I couldn't help it. Dean, I give you my word, everything I said was the truth."

Dean was silent for a few minutes, his mind spinning. "What's the plan for this demon?" he finally asked, trying to convince himself that he didn't believe him.

Crowley sighed, looking away. "My sources say he's in a meeting right now. He'll be available in about an hour. Then we act."

Dean nodded distractedly as he suddenly made a hard left, turning into a motel parking lot.

"Uh… Dean?" Crowley asked, looking up at the building.

Dean just opened the door and got out of the car. "Are you coming, or not?" He strode into the lobby without looking back, trusting that Crowley was behind him.

"Can I help you?" the bored-looking guy at the desk asked.

"Yeah, I need a room for an hour." That got some raised eyebrows as the man glanced between Dean and Crowley. "My friend here will pay." He turned to Crowley and almost laughed – Crowley, always so composed, was the picture of shocked, complete with wide eyes and agape mouth.

"Um, yeah…" Crowley recovered, stepping up to the desk. "Nicest room you have."


	4. Trust

It was funny how the knowledge of someone's real identity could make sex with them so different. For one thing, there was a weight in Dean's stomach that hadn't been there in the past, but mostly it was just difficult to stop himself from calling out the name Roderick. He had to repeatedly remind himself that this was Crowley, a demon, and he certainly wasn't calling out a demon's name, and so the weight in his stomach kept getting worse.

Crowley sighed as he rolled off of him, pressing his lips to Dean's neck. "I've missed this," he murmured.

Dean pulled away, pushing himself up without looking at the demon. "We need to get going."

There was a second's hesitation before Crowley responded. "You're right," he said reluctantly. He got out of bed as well, reaching for his clothes.

"And Crowley," Dean glanced back at him as he pulled on his pants. "Just to be clear, this never happened."

Crowley blinked, the words taking a second to sink in. "Excuse me?"

"Nothing has changed. You're still a demon, I still hate you, and once we no longer need you, I will be more than happy to kill you." He still wasn't entirely sure why he had decided to sleep with him again in the first place. Maybe it was to get it out of his system, or to give Crowley a taste of being toyed with, or maybe he just hadn't made up his mind yet. It didn't matter, though; he was now sure of himself, and nothing could change that.

Hurt flashed across Crowley's face for just a moment before his expression turned cold. "You know, Dean…" He snapped his fingers and was once again dressed. "It's normally more polite to say those kinds of things  _before_  sex – just so that your partner doesn't get the wrong idea. Not that it matters to me one way or the other, so long as it never does happen again. So let's move it along, we still need to discuss the plan – I've made some changes from the original, which I think will make it go a lot smoother."

As it turned out, the changes weren't so much to make it go smoother, but rather to get some revenge on Dean. Crowley eventually stopped the demon, but not before he had given Dean quite the beating.

"Bastard," Dean muttered as they loaded the unconscious demon into the back of the car.

"I am astounded by your comebacks, truly."

"We were down there for ten minutes! You really expect me to believe you couldn't have stopped him sooner?"

"Oh, of course I could have," Crowley chuckled as he climbed into the back seat. "But that would have meant missing out on the show."

Dean shook his head as he started up the car. "Wow, I didn't know demons were so temperamental when it came to breakups."

"Not at all, darling; I just don't like being used and thought that you needed to be taught a lesson."

"You need a… lesson."

Crowley rolled his eyes. "Just drive, Dean."

Dean didn't want to admit it, but he honestly wasn't sure if they would have been able to get Pestilence's location if it weren't for Crowley. Of course, if he were asked, he would immediately say that he and Sam would have been able to get the information from the demon, but whether that was the truth was doubtful, largely because the demon was Sam's friend from college and Sam had a hard time staying level-headed around him. Not that Dean blamed him; finding out that someone close to you was a demon could do that to you. The difference was, Sam killed Brady, while Dean let Crowley walk away. He wasn't sure why he did it – maybe because he knew that they might still need him, but he knew deep down that that wasn't the only reason.

Still, he never wanted to see the demon again. And once again, he saw him far too soon. The very next day he appeared in Bobby's house, after apparently having talked the elder hunter into selling his soul for Death's location. In that moment, Dean truly felt angry enough to kill Crowley despite everything. Of course, then the demon had to go and prove his usefulness yet again by finding out about the Croatoan virus that Pestilence had ready to distribute to all of America in the form of a flu vaccination.

"How are we supposed to kill Death and stop the Croatoan virus?" Sam asked of no one in particular.

"By splitting up, obviously," Crowley said with a shrug.

"That's spreading us a little thin, don't you think?" Dean questioned without looking at the demon.

"Is there another option? Assuming you don't want the world to turn into the Walking Dead, that is."

Dean sighed, running a hand over his face. Why did the bastard have to be right about everything? "So how do you suggest we do this? Two take Death, three take the Croatoan?"

"Sounds fair."

"Why is he making the calls?" Sam demanded.

"Because I'm clearly the only one smart enough. Look, I've got Death's location. One of you boys come with me, and the other team up with feathers and wheels to stop the virus."

Dean made eye-contact with his brother, not wanting to go off with Crowley again, but even more so not wanting Sam to. "I'll take Death," he muttered.

"You sure?"

He hesitated just a second before nodding firmly. "Yeah. How hard can it be?"

"Well, then." Crowley clapped his hands together, though there was irritation in his eyes. "I'll let you tell the others the plan and meet you at dusk." He vanished before anything more could be said.

"You really trust him?" Sam asked, concern coloring his voice.

"No," Dean answered honestly. "But we need him. And we all want the same thing here."

"I hope so."

"If he wanted us out of the way, he would have done it by now. What he's doing makes no sense unless he really does want Lucifer out of the picture." Of that he was certain, at least.

"Letting a demon have free reign like this, though…"

"He doesn't. He's on a leash and I have no problem choking him with it."

"You sure?"

"Positive. I won't let him pull anything over on me." Not again. "But enough of this. This is the best plan we're going to get. Let's tell Bobby and Cas."

Surprisingly, the two of them agreed to it with little debate, and so a few hours later found Dean in the Impala alone with Crowley, yet again. His mind was back at Bobby's, though, recalling the exchange before they had parted ways.

"You just going to sit there?" Crowley had asked Bobby. And then Bobby had gotten to his feet as though he had never lost the use of his legs. Crowley explained it away by saying he had added it into Bobby's contract because he had wasted the deal, but Bobby hadn't asked for that, Crowley hadn't had to do it.

"Why did you do it?" he asked after about twenty minutes of silence.

Crowley turned away from the window with raised eyebrows. "Unless you're talking to yourself, you're going to have to be a little more specific."

"Bobby."

"Someone should really teach you complete sentences. Why did I give him his legs back? Because he's a lot more useful this way. How much use do you think he would be back there if he were still stuck in his wheelchair? I did us all a favor."

"But why do you even care about the Croatoan virus? It's not like it really has any bearing on if we stop Lucifer."

"I think it would be a bit more difficult for us if we had to fight zombies everywhere we went. Really, did you ever even go to school?" he snapped.

Dean glared at the road. "I just figured you would like a demonic virus."

"You thought wrong. It's messy and in poor taste. And I would like for the world to keep spinning for a little bit longer, something that will be hard once the virus has turned every living being into mindless killers."

Dean shook his head slightly. "You have got to be the weirdest demon there is."

"I am the smartest demon there is."

Dean snorted. "Right. So why aren't you in charge of things, then?"

"Maybe I will be someday."

"Assuming I don't kill you first."

"Don't make empty threats, Dean. It's a bad look for you."

"Who says they're empty?"

"Your eyes."

"You don't know my eyes very well then, because this threat ain't empty."

Crowley regarded him thoughtfully for a moment. "Dean, I can think of three reasons off the top of my head as to why you won't kill me. Would you like to hear them?"

"Oh yeah, I'd love to. This'll be good."

"One, you wouldn't have been able to get this far without me, you owe me. Two, if you were going to kill me, it would have been in a fit of rage once you found out I'm a demon. And three, you're still confused about your feelings for me."

"All of that is bullshit. We don't need your help, I can control my anger better than that, and the only feeling I have towards you is hatred."

"Does it help? Saying it out loud?"

"You know what, Crowley? How about you shut up before I shut you up?"

He shrugged. "Fine. I was content to sit in silence. You're the one who started talking. And the one who volunteered to come with me, mind you."

"Yeah, and that was definitely not because I want to be around you. I just didn't want you saying anything to Sam."

"I wasn't going to."

"And I don't trust you."

"Clearly. You're so determined not to trust me that you can't see what's right in front of you."

"What was that you said earlier about sitting in silence? Because I think that's the best thing you've ever said."

Crowley glared at Dean through narrowed eyes for a moment before returning his focus to the side window, not saying another word until they reached Chicago. Unfortunately, that left Dean nothing to do but think. At least when the demon was talking, he was generally pissing him off – now Dean was having a hard time controlling the thoughts that entered his mind. Death, he was going to kill Death, he started repeating the words to himself, occupying his mind with the mantra.

Except he didn't end up having to kill Death. The horseman handed his ring over willingly, showed him how to work it, and agreed to leave the city unharmed, all in exchange for Dean making the worst promise he could imagine. He had to let Sam say yes to Lucifer, let him throw himself into the cage and the devil along with him. Satan would be gone, but so would Sam.

Nothing could have prepared him for it, the emptiness he felt the second Sam leapt into the pit. Cas healed all of his physical injuries, but he almost couldn't feel a difference. It was a while before he was able to stand, and then he got into the Impala and just drove. He had promised Sam that he would live a normal life with Lisa, and he was clinging to that promise. Because without that he had nothing, there was no reason for him to go on.

"Dean."

He didn't even flinch as the soft voice spoke from the passenger's seat that Cas had vacated just a few minutes ago. He glanced over at Crowley with dead eyes, not saying anything.

Crowley studied him a bit, his expression almost concerned. "Where are you going?"

Dean meant to tell him that it was none of his business, but he suddenly realized that he was already speaking. "Lisa's. We dated a long time ago. Last time I went by, it seemed like she would take me back. I don't know if she still will, but I have to try."

"Why her?"

"Sam. He made me promise."

"So you're getting back with an old fling because it was your bothers dying wish?"

He didn't have a good answer to that, so he changed the subject. "What are you even doing here?"

"Making sure you're okay."

"Like you care."

"I do." There was so much conviction in his voice that it was hard for even Dean to argue with it.

"Well, thanks, but I'm fine. Certainly don't need the comfort of a demon."

Crowley hesitated before turning away. "Of course. I wish you luck on your life, Dean, since I wager I won't be seeing you again. Goodbye."

He vanished without another word, and Dean was surprised to realize that he could feel even more alone.


	5. Thinking

Living a normal life sounded easy – a job, a girlfriend, a kid (okay, that part hadn't sounded easy, but it wasn't like having to take on the Devil again) – but Dean wasn't prepared for what giving up  _his_  life would feel like. He went to work, maybe went out for some beers with the guys, came home, had dinner with Lisa and Ben, maybe watched a movie or played a game, went to bed, then did it all over again the next day. It was routine, it was simple, but he didn't feel like himself and he was beginning to wonder if it was possible to go insane from normalcy.

"Dean, where are you going?"

Lisa had walked into the living room to see Dean pulling on his jacket and grabbing his keys. Honestly, he didn't know where he was going, he just knew he had to go  _somewhere,_  do  _something._

"A bunch of us are off tomorrow, so Brian's throwing a late-night poker game." He felt bad for lying to her, but he wasn't even sure of what the truth was himself.

She frowned slightly. "Don't gamble away too much."

"Hey, don't worry, I'm awesome at poker." He took a few steps forward to give her a quick kiss on the cheek before walking out the door.

He ended up driving to a secluded spot in the country, deciding that he just needed a place to be alone. He sat on the hood of his truck and looked down from the cliff at the town below. The town that he lived in, worked in, had a life in. It was something he had thought he wanted, but now that he had spent close to a year living like this, he wasn't sure how much longer he could go on.

"Dean?"

Dean spun around, his heart pounding in his chest as he heard the surprised voice behind him. "What the hell are you doing here, Crowley?" he demanded.

The demon blinked a few times, working to conceal the surprise from his face. "I could ask you the same question."

"I live here."

"Really? Here? On this cliff? That's funny, because I come here a lot, and I've never seen you here before."

Dean was even more confused by that. "Why would you come here a lot?"

Crowley hesitated just a second before answering. "To think. It's a good place for it."

"Right…. And the place you go to think just happens to overlook he town where I live?" Dean highly doubted that that was a coincidence, and it made him uneasy.

"I'm not spying on you, if that's what you think."

"What are you doing, then?"

"I just like it here," he said defensively.

"To think? What do you even come here to think about?"

"That's personal. What have  _you_  come here to think about? Since I assume that's what you're doing here."

"Nothing."

"Well, I suppose that's not surprising." He walked over, leaning against the hood of the truck, beside Dean, glaring at the view in front of him with his arms crossed over his chest.

"Do you mind?"

"This is  _my_  spot. If anyone should leave, it's you."

"Well, I ain't leaving." No way was he giving into him.

"Fine. We'll both stay, then."

"Fine." Dean crossed his arms and turned his attention back to the view.

What the hell was he doing? He was standing out here with a  _demon,_  and a demon that he used to sleep with, at that. But at the same time, it almost felt reassuring, like he had a bit of his old life back. How twisted was that?

"So, how's the 'normal life' working out for you?" Crowley asked eventually.

"It's great," Dean answered without looking at him.

The demon hummed skeptically. "Yes, I suppose that's why you're out here."

"What's that supposed to mean?"

"It's written all over your face, Dean. You're not happy, and you've come out here to sort things out. Maybe I can help you."

"Are you seriously trying to make a deal with me?" His head snapped towards Crowley, his expression incredulous.

"What? No! I meant I'm someone who actually knows the real you. I can help you figure things out."

"Someone who knows the real me? You don't know me, Crowley!"

Crowley looked at him, eyebrows raised in disbelief. "I know all your favorite music, movies, food. I know you hate getting up in the morning, unless it means a good breakfast – even if you are the one to cook it, because you love to cook. I know the smile you get when you're embarrassed, and exactly what to say to see it. I know that you spend your life trying to live up to everyone else's expectations of you, and you can't step back for two seconds to see how amazing you truly are. I know what you look like when you're happy, and I know the look in your eyes right now, and it's not happiness."

Dean was speechless. He tried not to think about just how close he and Crowley had been before he learned who he really was. At the very least, he tried to pretend it was just sex. But it hadn't been, and Crowley's words served to remind him of that.

He cleared his throat uncomfortably, just wanting to change the subject. "Why are you up here, Crowley?"

"Honestly? Because I want to be close to you, and this is as close as I can get."

Dean felt a strange combination of emotions, suddenly remembering just how genuine the demon had sounded the last time they had spoken.  _Could_  he be telling the truth about his feelings? Surely not, but… it was starting to get hard to argue.

"What do you think about?" His tone was softer now, more sincere.

"Ah-ah, Dean. It's your turn to answer questions. What's bothering you?"

"Right now, you," he muttered, but there was no venom in his words. He glanced at the demon and sighed. "I don't even know. I have a great life, but… every time I get two seconds to myself, all I can think of is my old life. And it's not just missing Sam, it's everything. I feel too stationary, trapped. I've always wanted a home, but now I feel like I have to keep moving."

Crowley waited a second after Dean finished, making sure he didn't have anything else to add, before speaking. "This isn't your life, Dean. You're playing house, and it's not really you. There's nothing wrong with admitting that. You need to move on."

"Yeah, but this is the way things have to be. And I think it'll get better with time, but instead I just feel more suffocated every day."

"Why is it the way things have to be? You fought for free will, didn't you? Walk away."

"I promised Sam…"

"Yes, and I'm sure he thought that you would live happily ever after and find that this has always been the life you were supposed to live. But he was wrong."

Dean shook his head. "I have to make it work."

"No, you don't!" He turned to face Dean more fully. "Sam would want you to be happy."

"I just… can we talk about something else?" Dean really didn't know what to do. Crowley made some good points – great points, actually, points he couldn't argue with, but he couldn't break the last promise he had made to Sam before he had died. And Lisa was a great woman, and Ben really was like a son to him. There was no reason why he couldn't make it work.

Crowley sighed, nodding his head. They were both silent for a few moments before he spoke up again. "So, I see you traded in cars… trade in for a better taste in music, while you were at it?" He looked over at Dean with a smirk.

Dean threw his keys at him, making him laugh. "You're giving me your truck? Thanks, but I won't be caught dead driving that."

"You know, I could arrange that – your death, not you driving the truck."

"Nah, I bet you're rusty."

"I could still take you."

"Whatever helps you sleep, love."

They stayed out there for several hours talking about anything that popped into their minds. Dean didn't want to admit it, but it was nice. Actually, it was the best he'd felt in several months. He looked at his watch and cringed when he saw that it was one in the morning.

"Damn… I need to get home, Lisa will be worried."

Crowley looked down, but not before Dean caught the hurt look in his eyes. "You're going back, then?"

"I have to."

"You really don't."

"For me, I do."

He climbed into his truck and started it as Crowley moved to stand to the side. Dean rolled down his window, sticking his head out slightly. "You never did tell me what you came out here to think about."

Crowley gave a small smile. "Maybe next time."

Dean nodded, knowing full well that neither of them expected there to be a next time. "See ya, Crowley."

Dean drove away, feeling almost like a weight had been lifted off his shoulders. He knew talking to a demon for hours shouldn't make him feel like that, but it had been like getting a piece of his old life back. It had been what he needed. He just hoped this feeling would last.


	6. Admittance

He really should have known better. The peace of mind that had come from talking to Crowley kept Dean going for a week before everything started to fall apart again. When he went back to the same spot on the cliff, he tried to tell himself that it wasn't because he was hoping to see the demon. It was just to think, the same as the last time. The longer he sat out there, though, the harder it became to convince himself. And by the time he had sat there for an hour, turning his head at every sound, he began to give up hope.

He sighed as he got back into his truck, feeling even worse than he had when he had come out here.

"Don't leave on my account."

Dean spun around, catching himself on the door as he half-slipped out of his truck. "I was starting to think you weren't coming tonight."

Crowley's amused smirk slipped from his face, his eyes widening slightly. "You're here to see me?"

"I… no, I just… figured if you _were_ coming, you'd be here by now." He knew it was a worthless excuse that Crowley would see right through, but thankfully, he didn't press it.

"I had things to do." He took a couple of steps toward Dean. "Will you stay for a bit?"

Dean couldn't help but give a small smile. "Why not? I don't have anywhere else to be." He stepped out of his truck, shutting the door behind him.

It became a weekly thing, meeting Crowley at the cliff. Dean felt a little guilty, but it wasn't like he was actually cheating on Lisa. All he and Crowley did was talk, and he always came away from it feeling better. It was what kept him going.

"Are things getting any better for you?"

It was a couple of months since they had started their weekly meet-ups, and they were laying in the back of Dean's truck, Dean looking up at the sky while Crowley watched him.

"Yeah."

"Really?"

Dean could hear the skepticism in Crowley's voice and he sighed. "Yes, really. I've been feeling a lot better lately."

"You know, when I ask that, I'm asking about your actual fairy tale life, not our secret meetings."

"What does it matter, when it's still part of my life?"

"Because it's not, really. I'm just a small piece of your past that you can escape to once a week."

"Well, it's still the highlight of my week."

Genuine surprise showed on Crowley's face and Dean froze as he realized what he had just said.

"I just mean… I enjoy it."

"I know what you mean, Dean, and it's very telling."

"Drop it, Crowley."

"Why can't you allow yourself to do what you enjoy, for once?"

"I'm here, aren't I?"

"Yes, but for how much longer? Why go back when it's not the life you want?"

Dean turned his head to look at Crowley more directly. "You know why."

"And I still say that's not a real reason."

"So what do you want me to do? Leave Lisa? Run off with you?"

"I want you to be _happy."_

"Well, I am."

"You're lying!"

"I have to, Crowley! I can't very well say that I'm happier with a demon than my very sweet girlfriend, who has completely altered her life to be there for me!"

"Then why do you even come out here, Dean?"

Dean took a deep breath, looking away from Crowley. "Great question." He pushed himself up into a sitting position. "Goodbye, Crowley."

"No, wait, Dean. I didn't mean that." Crowley hastily sat up, catching Dean's hand before he could get out of the truck bed.

"Doesn't matter. You're right."

"Dean, please, I'm sorry. Can we just forget this entire conversation?"

Dean was about to say no, but he made the mistake of looking Crowley in the eyes and he caved. "Fine."

"Thank you." Crowley glanced down to where his hand was still wrapped around Dean's. Neither of them moved. "I never answered your question from the first time I found you out here."

"And what question was that?"

"What did I come out here to think about?"

"So, what's the answer?"

Crowley took a deep breath before looking back up to meet Dean's eyes. "You."

Dean didn't know who kissed whom, but suddenly their lips were moving against each other, passionate and desperate. They fell back to the bed of the truck, Crowley's hands clutching at Dean's back, and one of Dean's hands gripping Crowley's short hair while the other ran along his side. Dean didn't know how long the kiss lasted, maybe a minute, maybe thirty, but when he finally pulled back, he was panting.

"Dean…" Crowley breathed.

Dean pushed himself up and nearly completely out of the truck bed, his legs dangling over the edge. "I should go," he muttered, his voice rougher than usual, his eyes locked on the ground.

"Dean-"

But Dean was already up and climbing into the cab of the truck. Crowley materialized beside him, placing a hand on the door to keep him from closing it.

"See you next week?" The worry was obvious in Crowley's voice and Dean felt an ache in his chest.

"I don't know," he answered honestly, attempting to close the door.

Crowley sighed and stepped back, watching Dean drive off.

The more Dean thought out it, the surer he was that he would not be going back. What had he been thinking? He had a girlfriend, he couldn't go about kissing demons. Meeting with Crowley at all had been a mistake, one that he had to put a stop to now.

It was an easy concept in theory, but without Crowley, his life began to weigh on him again. One week later and he felt worse than he had felt even before he had started meeting with Crowley. Two weeks later and he was at a breaking point, with which came a sort of clarity.

All along, he had known that Crowley had been right, and now he no longer saw the point in attempting to deny it. He knew what he wanted, and as great as Lisa and Ben were, as much as he truly cared about them, it wasn't them. Surprisingly enough, Lisa understood, and she responded with a calmness that made Dean wonder how long she had been expecting this conversation. He didn't have much to pack up, and so an hour later he was back in his Impala and on his way to his and Crowley's spot, hoping the demon would be there.

As he pulled into the outlet, the demon turned around, blinking in surprise.

"Dean-"

Dean didn't let him get anything else out. He had jumped out of the car and pressed Crowley against the side, his lips crashing against his before the demon had a chance to comprehend what was happening. Crowley returned the kiss eagerly and Dean's hands slipped between them, pulling at the buttons of Crowley's jacket. When Crowley realized what Dean was doing, though, he pulled back, his hands resting on his shoulders.

"Dean, I am _not_ having sex with you out in the middle of the country. There's no telling what sort of things are out here; I could get bit by some poisonous creature and die."

"You can't die from poison," Dean pointed out.

_"_ _You_ could, though. Besides, I have more class than this."

Dean rolled his eyes. "What do you suggest, then?"

Crowley smiled as he brought a hand up and snapped his fingers. The next second, the two of them stood in a lavish bedroom, furnished in black and red. "What do you think?"

"Where are we?"

"My place."

"I thought Lucifer burnt your house down."

"I got a new one, obviously."

"It's nice. A little… show-offish…. It suits you." He smirked.

"You know, Dean, just because I'm not as cheap as you, it doesn't mean I'm – 'show-offish.'"

"I'm not cheap! Hunting just doesn't pay well."

"I thought you weren't a hunter."

"I'm…" Dean sighed. "I guess I don't know anymore."

Crowley scrutinized Dean for a second, then walked over to sit on the edge of the bed, patting the space beside him. "What's going on with you, Dean?"

Dean sat down beside Crowley, staring into space for a few seconds before speaking. "I wasn't going to come back. I was sure of it this time. But… I missed you. It wasn't the life weighing on me anymore. Sure, I still prefer hunting to the way things are now, but that wasn't what was bothering me. I just want to be with you, whatever life I'm leading."

It was probably one of the hardest things Dean had ever admitted, but it was also one hundred percent true. He could be happy doing just about anything, as long as he was coming home to Crowley.

He felt Crowley's hand on his cheek, turning his head to face him. "That can be arranged," he said softly, before kissing him passionately.

The kiss started out soft and fervent, but it quickly became more rough and desperate. Crowley grabbed tightly at Dean's hair as he pushed him back onto the bed and straddled him, both of them kicking off their shoes as they fell back. The last time that the two of them had slept together, the only time that Dean had been aware of Crowley's true identity, Dean had been determined for it to mean nothing, for it to be the last time for them. This was completely different. Now they were both being one hundred percent honest to each other, and it wasn't the end, it was the beginning. Somehow these simple changes made everything so much more amazing.

"Crowley?" Dean murmured as he curled into the demon's side, his breathing slowly returning to normal.

"Hmm?" Crowley hummed as he stroked his hand through Dean's hair.

Dean held his breath as he struggled to figure out exactly how he wanted to word his question. "Do you… I mean, you've sort of made it seem as though you honestly care about me… and maybe even a little more than just that… But do you, really? Is that even possible for you?"

Crowley was silent for a few seconds, and as much as Dean wanted to look up to see his expression, he was scared of what it might be. When Crowley spoke, his voice was hesitant and pensive. "Demons rarely fall in love. It is something that we try to avoid, as a general rule. It is a dangerous weakness, and beyond that, it just ruins our reputations. It does happen, though. I know of only a small handful of demons who have fallen in love – always with other demons. I have never heard of a demon falling in love with a human, or any other species. Of course, I don't imagine that they would advertise it, even if they did. I can only imagine what other demons would say, and I can't see everyone making it out alive in order to live out their happily ever after…." Crowley sighed. "That being said, I am very hesitant to admit my feelings for you. But… I am very powerful and do hold a fair amount of sway, so… it's your choice if it's worth the risk."

Dean pushed himself up, off the demon's chest, in order to look him in the eyes, searching the hazel depths for some kind of sign. At this point, there was no more denying how he felt about Crowley; he just had to decide if pursuing what he wanted was worth risking his life for, and if he could truly trust a demon to return his feelings. And what he saw in Crowley's eyes was the same look he had worn so many times that he had looked at him; the look that, while they were dating, Dean took as assurance that their relationship _did_ mean something to the both of them; the look that, after Dean had learned the truth, he tried to pretend he didn't see. It was a look that he had a hard time not trusting, and now he had no desire to doubt it. Because as long as Dean was right in this, he had no doubt that Crowley was worth the risk.

Dean drew in a deep breath, his gaze growing determined. "I love you, Crowley."

Crowley let out the breath that he had been holding, his wide eyes making it obvious that he hadn't expected Dean to say the words aloud. Dean caught the smile that was just starting to form before Crowley leaned in and kissed him softly. "Good," he murmured as he drew back.

Dean raised his eyebrows. "Good? That's it?"

Crowley blinked. "You aren't going to actually make me say it, are you?" he demanded indignantly.

"Yeah, yeah, I am!"

"Dean, I think that's all pretty well implied. _Surely_ you don't need to hear the words."

"I'd like to. Why won't you just say it?"

"Because I'm a demon! It's embarrassing!"

"It's embarrassing to admit that you love me?"

"Yes!"

Dean just glared at him for a moment before shaking his head and pushing himself away. "Fine, if this is so _embarrassing_ for you, how about I just leave? I'd hate to be any kind of burden on you, after all."

Crowley groaned. "You're insufferable, you know that?" he snapped.

Dean turned back towards him with a slight smirk. "Is that all?"

"No," he sighed, running a hand over his face. "I love you," he mumbled into his hand, the words barely audible.

"What was that?" Dean pressed, his smirk growing.

Crowley's head snapped up, his eyes focusing on Dean in a glare. "I love you," he growled so vehemently that Dean couldn't help but laugh.

He cupped either side of Crowley's face in his hands and pulled him into a longer kiss. "I suppose I'll stick around, then."

**Notes for the Chapter:**

> I thought this concluded the story nicely; however, there is still more to tell, involving the plot line of season 6. If everything goes as planned, I will likely to writing a second part to this story after I get caught up on my other works. I have no idea when that will be, so keep an eye out.


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